When evaluating markets for rental properties, there are a lot of factors to consider: population growth, employment rates, rent to price ratio/GRM/Cap Rate, rent trends, vacancy rates, etc. 

.- >65K in rent collected- having someone to bring in Amazon packages when it is raining outside- generally having someone to watch over the property when out of town oftenI think the headache is worth it.

At the time of purchase, I knew I might not want to stay indefinitely and at some point to might convert the home to a rental property.

You can pay for expediting for plan reviews and the best way to "expedite" beyond that is to make sure that your engineer / consultants are submitting complete packages each review cycle.

We want to get a Vacation Rental Permit for stays under 30 days for ADU but current zoning doesn't allow it.

In Pittsburgh it’s the only way to buy rentals haha!

Do you think a duplex is generally a better investment than a single-family home for rental purposes?

I was just telling my friend today that I'm getting multi-family, high performance, and relationship mentoring all in one package! 

A knowledgeable attorney can advise here.Create a solid operating agreement: Since you own the condo with a friend, a clear operating agreement is essential to outline responsibilities, decision-making, and profit-sharing for the LLC.To save on costs:Look for real estate attorneys who specialize in investment properties and might offer package deals for the retitling, operating agreement, and filing the LLC.Shop around for title companies that can handle the transfer smoothly and provide competitive rates.Research DIY options for setting up the LLC if your situation is straightforward, though I’d still recommend a lawyer for the transfer process itself.Good luck with the process!

Why do you want to buy 2 rentals a year?